2-Methylsulfanyl-5,6,7,8,9,10-hexahydro-cycloocta[b]pyridine-3-carbonitrile | 154384-05-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-Methylsulfanyl-5,6,7,8,9,10-hexahydro-cycloocta[b]pyridine-3-carbonitrile
• 英文别名: 2-Methylsulfanyl-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carbonitrile
• CAS: 154384-05-1
• 化学式: C₁₃H₁₆N₂S
• 分子量: 232.349
• InChiKey: FZUXLNBIOBKNLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  62
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Methylsulfanyl-5,6,7,8,9,10-hexahydro-cycloocta[b]pyridine-3-carbonitrile 在 间氯过氧苯甲酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以45%的产率得到2-Methanesulfonyl-5,6,7,8,9,10-hexahydro-cycloocta[b]pyridine-3-carbonitrile
  参考文献：
  名称：

  A convenient synthesis of 5-deaza nonclassical antifolates: Reaction of cyanothioacetamide with sodium salts of 2-(hydroxymethylene)-1-cycloalkanones

  摘要：

  Condensation of cyanothioacetamide with sodium salts of 2-(Hydroxymethylene)-1-cycloalkanones afforded the corresponding pyridine-2(1H)-thiones 4. Compounds 4 served as a key intermediates for the synthesis of condensed 2,4-diaminopyrido[2,3-d]pyridines 7. Compounds 7 were of interest as potential inhibitors of dihydrofolate reductase.

  DOI：

  10.1016/s0040-4020(01)80745-6
• 作为产物：
  描述：

  sodium (2-oxocyclooctylidene)methenolate 在 sodium hydroxide 、 哌啶乙酸盐 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.17h， 生成 2-Methylsulfanyl-5,6,7,8,9,10-hexahydro-cycloocta[b]pyridine-3-carbonitrile
  参考文献：
  名称：

  A convenient synthesis of 5-deaza nonclassical antifolates: Reaction of cyanothioacetamide with sodium salts of 2-(hydroxymethylene)-1-cycloalkanones

  摘要：

  Condensation of cyanothioacetamide with sodium salts of 2-(Hydroxymethylene)-1-cycloalkanones afforded the corresponding pyridine-2(1H)-thiones 4. Compounds 4 served as a key intermediates for the synthesis of condensed 2,4-diaminopyrido[2,3-d]pyridines 7. Compounds 7 were of interest as potential inhibitors of dihydrofolate reductase.

  DOI：

  10.1016/s0040-4020(01)80745-6

文献信息

• Regioselective synthesis of 5,6-polymethylene-3-cyanopyridine-2(1H)-thiones and fused heterocycles based on them
  作者：L. A. Rodinovskaya、E. V. Belukhina、A. M. Shestopalov、V. P. Litvinov

  DOI：10.1007/bf01169725

  日期：1994.3

  6-polymethylene-3-cyanopyridine-2(1H)-thiones which were regioselectively alkylated at the sulfur atom by alkyl halides. Derivatives of 3-cyanopyridine-2(1H)-thione and 2-alkylthio-3-cyanopyridine were used for regioselective synthesis of substituted heterocycles: 3-aminothieno[2,3-b]pyridines, pyrido[2,3∶2′,3′]thieno[4,5-d]pyrimidines, and pyrido[2,3∶2′,3′]thieno[4,5-d]oxazines.

  2-羟基亚甲基环戊烷-1-酮或-环辛烷-1-酮钠盐与氰硫代乙酰胺缩合得到5,6-聚亚甲基-3-氰基吡啶-2(1H)-硫酮，其在硫原子上被卤代烷区域选择性烷基化。3-氰基吡啶-2(1H)-硫酮和2-烷硫基-3-氰基吡啶的衍生物用于区域选择性合成取代杂环：3-氨基噻吩并[2,3-b]吡啶、吡啶并[2,3∶2'、 3']噻吩并[4,5-d]嘧啶和吡啶并[2,3∶2',3']噻吩并[4,5-d]恶嗪。